Based on Bowlby's and Ainsworth's theories of attachment, this study sought to determine whether incoming college freshmen who were securely attached to their mother and/or father would make more positive academic persistence decisions and would perceive less academic stress. In addition, their separation-individuation from their parents and how this was related to their academic persistence decisions and stress were examined. Students in a summer program designed to bridge high school and the university were invited to participate. Of the 170 students in this program, 163 completed the survey packet that consisted of an informed consent letter, a demographics questionnaire, the Parental Attachment Questionnaire, the Inventory of Parent and Peer Attachment, the Psychological Separation-Individuation Inventory, the College Stress Scale, and the Persistence/Voluntary Dropout Decisions Scale. Analyses of the data revealed that secure attachment to parents was positively related to more positive persistence decisions and to less academic stress. Particularly, father attachment was a significant predictor of stress. The correlation between each attachment variable (mother, father, and parents) and stress was negative. When separation-individuation was examined, the emotional independence from mother and from father and functional independence from mother and from father were not statistically significant predictors of persistence decisions. However, when a post hoc analysis was conducted on each parent individually, separation-individuation from mother was related to academic persistence decisions. Finally, the males and females were compared on levels of separation-individuation. The significant multivariate analysis of variance was investigated with a discriminant analysis, which revealed that the most powerful discriminator between males and females were functional independence from father and from mother and emotional independence from mother. These findings are discussed in light of theory and ideas for counseling interventions for incoming freshmen.